This is the scenario I see. Original roster players in bold.
Offer A
dwoolery
27 y.o.superstar ss
non-challenge owner
19 y.o. potential superstar ss
26 y.o SP1
Offer B
dwoolery
27 y.o.superstar ss
34 y.o. former superstar 1b, in final year of 5yr/$20m contract, still good but not $20m good
challenge owner
34 y.o. former superstar 1b, in final year of 5yr/$10m contract, not quite as good as above
39 y.o. dh, $8m, included mainly for payroll reasons
26 y.o SP2
From an HBD perspective, Offer A seems better, but for challenge purposes, you may go with Offer B. I guess you could accept A and just release the 1b, but that would leave a hole in you lineup, and again, you'd probably only do this if the non-challenge offer was much, much better, which was the issue I was raising in the first place.